Method of sterilizing anthers

ABSTRACT

The present invention relates to the art of agriculture. The method of sterilizing anthers of plants comprises treatment of the plants with a sterilizing agent in combination with a diluent during the period of the fifth and/or sixth stage of organogenesis. According to the invention, as the sterilizing agent use is made of derivatives of phosphoric acids of the general formula: ##STR1## wherein R is H, a C 1  -C 4  alkoxy, dimethylamine, wherein X is O, NH; B is H, a C 1  -C 4  alkyl, phenyl, D is H, CH 3  ; A is a C 1  -C 4  alkyl, phenyl furyl; R&#39; is OH, ONH 4 , OAlk(C 1  -C 4 ), phenyl; R 2  is a C 1  -C 4  alkyl, NaNH 4 , NH 3  Alk(C 1  -C 4 ), NH 2  Alk 2  (C 1  -C 4 ), or mixtures thereof. The method according to the present invention is useful in selection and seed production.

FIELD OF THE ART

The present invention relates to the art of biology and agriculture and, more particularly, to a method of sterilization of anthers which is useful in selection and seed production.

PRIOR ART

At present the world is facing the problem of intensification of the agriculture, in particular, of raising yields of grain crops, fodder, vegetable and industrial plants by way of an extensive application of the firstgeneration hybrids. Due to the heterosis phenomenon these hybrids are distinguished from the parental forms by a higher productivity (by 25 to 30%) and by a high quality of the products. Known in the art is a method of breeding novel hybrids based on a "cytoplasmic male sterility-fertility reductants" system. This method is based on a longtime (taking 12-14 years) and complicated selection work involving the creation of sterile analogs, of sterility-fixing agents and fertility reductants. Most promising are methods based on sterilization of anthers by means of chemical sterilizing agents (gametocides). The use of gametocides proves to be much more economically efficient than the use of the "cytoplasmic male sterility" system, since there is no necessity in creating such forms as a sterile analog, an analog of sterility fixation in maternal forms and an analog of fertility reduction in paternal forms. It is practically possible to obtain seeds of first-generation hybrids both in the course of the selection studying of the initial forms and in the organization of their industrial production.

By now about 200 compounds have been found which display a gametocidal activity and belong to the different classes of chemical compounds as regards their chemical structure. Gametocides must cause complete male sterility in the treated plants, while preserving the viability of ovicells and ensuring setting in open pollination at a sufficiently high level (preferably, not less than 70% of the control). Their phytotoxicity and toxicity for the warm-blooded must be minimal.

Known in the art are methods for sterilizing the anthers of cereal crops (L.J.Nickell. Plant Growth Regulators. Application in Agriculture. Moscos, "Kolos" Publishers, 1984, pp. 28-31; SU, A, 906457) which comprise treatment of the plants with sterilizing agents such as 2-chloroethylphosphonic acid (Ethrel), maleic acid hydrazide, di-(polyfluoroalkyl)-phosphoric acid and salts thereof, and the like. The treatment of the plants with sterilizing agents is effected at the V or VI stage of the organigenesis (after F.M.Kuperman).

At the V-th stage of the organogenesis the processes of the formation and differentiation of florets begin. AT the end of this stage neoplasms originate: sporogenous archisporeal tissues. At this stage the initiation of the stamina, pistil and integumentary organis of the floret occurs. At the V-th stage the beginning of differentiation of the stamen primordium into a connective and pistil is observed. The VI-th stage is characterized by the process of the floret formation (micro- and macro-sporogenesis). At this stage individual mononuclear pollen grains are usually formed (F.M. Kuperman, "Morphophysiology of Plants", Moscos, "Vysshaya Shkola" Publishers, 1973, pp. 30-36).

Also known in the art is a method of sterilizing the anthers of gramineous plants (GB, A, 1,567,153) which comprises treating the gramineous plants with a sterilizing agent during the period between the appearance of the second internode and earing. As the sterilizing agent heterocyclic compounds are used, the main representatives thereof being 2-carboxy-3, 4-methanopyrrolidine or 2-methoxycarbonyl-3, 4-methanopyrrolidine. These compounds are used in combination with diluents and surfactants.

DISCLOSURE OF THE INVENTION

The present invention is directed to the provision, by selecting appropriate sterilizing agents, of a method enabling its application to sterilization of the anthers of a broad range of crops with a high efficiency of sterilization, while preserving a high settability of seeds in open pollination.

This problem is solved by that in a method for sterilization of the anthers of plants by way of treating them with a sterilizing agent in combination with a diluent during the fifth and/or sixth stage of the organogenesis, in accordance with the present invention as the sterilizing agent use is made of phosphoric acid derivatives of the general formula: ##STR2## wherein R is H, a C₁ -C₄ -alkoxy, dimethylamine, wherein X is O, MH; B is H, a C₁ -C₄ -alkyl, phenyl; D is H, CH₃ ; A is a C₁ -C₄ alkyl, phenyl, furyl; R¹ is OH, ONH₄, OAlk(C₁ -C₄), phenyl; R² is a C₁ -C₄ -alkyl, Na,NH₄, NH₃ Alk(C₁ -C₄), NH₂ (Alk)₂ (C₁ -C₄), or mixtures thereof.

The sterilizing agent can be used in combination with any known acceptable diluent. It is advisable to use it in combinations with water in the form of a 0.1-2% aqueous emulsion or a solution. As the plants to be treated with this sterilizing agent it is preferred to use gramineous plants of sunflower.

The method according to the present invention makes it possible to obtain a male sterility of the plants (98-100%) and to retain a high percentage of settability of seeds (above 70%). In order to ensure a high level of sterilization of the anthers under unfavourable climatic conditions, a repeated treatment of the plants with the sterilizing agent is effected during the periods of the fifth and/or sixth stages of organogenesis (after Kuperman).

PREFERRED EMBODIMENT OF THE INVENTION

The method according to the present invention is carried out in the following manner.

Plants such as winter and spring wheat, diploid and tetraploid rye, triticale, millet, sunflower and the like are treated with a sterilizing agent which represents phosphoric acid derivatives of the general formula: ##STR3## wherein R is H, a C₁ -C₄ -alkoxy, dimethylamine, wherein X is O, NH; B is H, a C₁ -C₄ -alkyl, phenyl; D is H, CH₃ ; A=a C₁ -C₄ alkyl, phenyl, furyl, R¹ is OH, ONH₄ OAlk(C₁ -C₄), phenyl; R² is a C₁ -C₄ -alkyl. Na, NH₄, NH₃ Alk(C₁ -C₄), AH₂ (Alk)₂ (C₁ -C₄), of mixtures thereof.

The derivatives of phosphoric acid can be used in combination with any acceptable diluents. It is advisable to use water as the diluent. It is preferable to use a 0.1-2% aqueous emulsion or a solution of the above-mentioned compounds.

When desired, any suitable surfactants can be added to the working solutions. Usually it is advisable to add, to the working solutions upon application thereof onto the plants, any known auxiliary additives such as wetting agents, dispersing agents, adhesives.

The sterilizing agent can be applied to the plants by various methods of treatment such as hydraulic spraying, air spraying (aerosols). The treatment of the plants with the sterilizing agent is carried out during the period of the fifth and/or sixth stage of organigenesis (after Kuperman). The does of the sterilizing agent depends on the nature of the compound, on the crop being treated, on the stage of the treatment and on the natural and climatic factors. In order to ensure a high sterilizing effect under unfavourable coimatic conditions, it is advisable to carry out a repeated treatment of the plants at the VI-th stage of organogenesis. The total dose of the sterilizing agent ranges from 0.6 to 20 kg/ha.

All the derivatives of phosphoric acids employed as the sterilizing agent according to the present invention have been tested for toxicity in experiments on animals. The results of the experiments have shown that these compounds are low-toxic or substantially non-toxic ones.

Thus the compounds according to the present invention such as monosodium phosphite, monomethylammonium phosphite, diammonium phosphite, monoammonium phosphite, methylammonobutyl phosphite, dimethylammoniummonomethyl phosphite, triethylphosphite, dimethylphosphite, diethylphosphite, diisopropylphosphite have the LD₅₀ =1,000-4,000 mg/kg of the animal's bodymass. All other derivatives of phosphoric acids have their LD₅₀ over 1,000 mg/kg.

The derivatives of phosphoric acids are obtained according to conventional procedures such as by way of reacting a corresponding carbonyl compound, an amine and a hyddrophosphoryl component, or by way of reacting alcohols with phosphorus trichloride, or by reacting a corresponding base with acidic components.

The present of gametocidal activity in the sterilizing agents according to the present invention has been revealed in field tests in different soil and climatic zones on 10 m² plots in 3- and 4-fold tiers. Each sterilizing agent has been tested for at least five years.

The occurrence of the organogenesis stages is controlled cytologically. The treatment of the plants with the sterilizing agent is conducted at the beginning of the fifth stage of the organogenesis after Kuperman.

In the course of earing, the main ears and other tiers are isolated by means of parchment isolators. For wheat and triticale individual isolators are used. For rye one ear from 5 to 7 different adjacents plants is brought under one common isolator. For millet each panicle is isolated individually. The percentage of sterility (X) for wheat, rye, triticale and millet is calculated according to the formula: ##EQU1##

The number of grains in the non-isolated ears of the control plants is assumed to be a 100% settability in open pollination.

To obtain reliable data, use is made of 20-25 isolators from each tier for wheat and triticale, 10-15 isolators from each tier for rye and millet.

To control the chemical sterilization of sunflower pollen, 45 treated plants on each tier are used for each compound; 15 plants out of them are isolated for open pollination; the heads of other 15 plants are pollinated with a mixture of pollen gathered on 20-25 treated isolated heads and 15 plants are left for open pollination with the view to check the settability of the achenes with the paternal-form pollen.

The male sterility of the plants of sunflower is assessed by the results of fertility and viability of the pollen, morphological features of spermatozoa and setting percentage of the achenes in pollination of the treated plants with the pollen from the non-treated paternal form. The viability of the ovicell is determined from the setting of seeds in the treated plants in open pollination with the paternal form.

The treatment of the plants should be preferably carried out in clear calm weather. All the compounds penetrate into the plant tissues within the period of 4 hours. In the case of rainfall during the 4-hours' period, it is necessary to retreat the plants at the VI-th stage of the organogenesis.

For a better understanding of the present invention the following examples illustrating the embodiments of the method according to the present invention are given hereinbelow.

EXAMPLES 1 to 12.

Plants of winter wheat of Mironovskaya 808 variety are treated at the V-th stage of organogenesis (after Kuperman) by spraying, from a knap-sack sprayer, with a 2% aqueous emulsion of the following sterilizing agents: diethyl-N-methyl-α-aminobenzylphosphonate, diethyl-N-phenyl-α-aminofurylmethyl-phosphonate, dimethyl-N-ethyl-α-aminobenzylphosphonate, dimethyl-N-methyl-2-aminofurylmethylphosphonate, diethyl-α-amino-α-methylpropylphosphonate, diethyl-N-methyl-2-aminofurylmethylphosphonate, diethyl-α-hydroxyfurylmethylphosphonate, diethyl-N,N-dimethylamidophosphate, diethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-α-aminoethylphosphonate, diethyl-N-ethyl-α-aminofurylmethylphosphonate, diisopropyl-N-methyl-α-aminofurylmethylphosphonate respectively.

As the emulsifying agent added is 0.1% by mass of calcium C₁₂ -C₁₄ -alkylbenzenesulphonate. The emulsion also contains, as the adjuvant, 0.01% by mass of dimethylsulphoxide. The rate of consumption of the preparation is 20 kg/ha. Serving as the control are the plants treated with the diluent without the sterilizing agent. The results of the tests are shown in Table I hereinbelow. Similar results are obtained in the treatment of the plants at the VI-th stage of the organogenesis.

                  TABLE 1                                                          ______________________________________                                                         Number         Number Percentage                                               of grains                                                                               Steri-                                                                               of grains                                                                             of setting                                               in ear   lity  in open-                                                                              in open                                        Example   under    percen-                                                                              pollina-                                                                              pollina-                                 No.   No.       isolator tage  tion   tion                                     1     2         3        4     5      6                                        ______________________________________                                         1.    Control   38.3      0.0  41.0   100.0                                    2.    Example 1 0.0      100.0 33.8   82.4                                     3.    Example 2 0.1      99.7  36.9   90.0                                     4.    Example 3 0.3      99.2  39.7   96.8                                     5.    Example 4 1.5      96.1  40.2   98.0                                     6.    Example 5 0.0      100.0 35.4   86.3                                     7.    Example 6 0.6      98.4  37.8   92.2                                     8.    Example 7 2.6      93.2  34.9   85.1                                     9.    Example 8 0.2      99.5  36.6   89.3                                     10.   Example 9 0.0      100.0 37.1   90.5                                     11.   Example 10                                                                               0.0      100.0 35.4   86.3                                     12.   Example 11                                                                               1.6      95.8  28.0   68.3                                     13.   Example 12                                                                               0.8      97.9  40.7   99.3                                     ______________________________________                                    

EXAMPLES 13 to 23

Plants of winter wheat of Priboy variety are treated at the V-th stage of organogenesis (after Kuperman) by spraying a 2% aqueous emulsion of the following sterilizing agents; diethyl-N-methyl-α-aminobenzylphosphonate, diethyl-N-phenyl-α-aminofurylmethylphosphonate, dimethyl-N-ethyl-α-aminobenzylphosphonate, dimethyl-N-methyl-2-aminofurylmethylphosphonate, diethyl-α-amino-α-methylpropylphosphonate, diethyl-N, N-dimethylamidophosphate, diethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-N-ethyl-α-aminofurylmethylphosphonate, diisopropyl-N-methyl-α-aminofurylmethylphosphonate respectively. As the emulsifying agent, 0.01% by mass of calcium C₁₂ -C₁₄ -aklylbenzene-sulphonate is added. The emulsion also incorporates 0.01% by mass of tetrahydrofuran as the adjuvant. The rate of consumption of the preparation is 12 kg/ha. Serving as the control are the plants treated in a manner similar to that described in Example I. The results of the tests are shown in Table 2. Similar results are obtained in the treatment of the plants at the VI-th stage of organogenesis.

                  TABLE 2                                                          ______________________________________                                                                                 Percen-                                               Number of        Number of                                                                              tage of                                               grains in Sterili-                                                                              grains in                                                                              setting                                               ear under ty per-                                                                               ear in  in open                                     Example   percen-   centage,                                                                              open pol-                                                                              pollina-                               No.  No.       tage      %      lination                                                                               tion, %                                1    2         3         4      5       6                                      ______________________________________                                         1.   Control   32.1       0.0   36.8    100.0                                  2.   Example l3                                                                               0.1       99.7   33.1    89.9                                   3.   Example 14                                                                               0.3       99.1   35.0    95.1                                   4.   Example 15                                                                               0.6       98.1   32.8    89.1                                   5.   Example 16                                                                               2.8       91.3   32.6    88.6                                   6.   Example 17                                                                               0.0       100.0  32.1    87.2                                   7.   Example 18                                                                               0.0       100.0  34.5    93.8                                   8.   Example 19                                                                               0.0       100.0  35.7    97.0                                   9.   Example 20                                                                               3.8       88.2   36.0    97.8                                   10.  Example 21                                                                               0.0       100.0  34.6    94.0                                   11.  Example 22                                                                               0.2       99.4   35.9    97.6                                   12.  Example 23                                                                               0.1       99.7   36.3    98.6                                   ______________________________________                                    

EXAMPLES 24-29

Plants of winter wheat of Polesskaya-70 variety are treated at the V-th stage of organogenesis (after Kuperman) by way of spraying, from a knap-sack sprayer, with a 2% aqueous emulsion of the following sterilizing agents: diethyl-α-hydroxyfuryl-methylphosphonate, diethyl-N, N-dimethylamidophosphate, diethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-α-aminoethylphosphonate, diethyl-N-ethyl-α-aminofurylmethylphosphonate, diisopropyl-N-methyl-α-aminofurylmethylphosphonate respectively. As the emulsifying agent 0.1% by mass of calcium C₁₂ -C₁₄ -alkylbenzenesulphonate is added.

The emulsion also incorporates, as the adjuvant, 0.01% by mass of dodecylsulphate. The rate of consumption of the preparation is 16 kg/ha. Serving as the control are the plants treated in a manner similar to that described in Example I hereinbefore.

The test results are shown in Table 3 hereinbelow. Similar results are obtained in the treatment of the plants at the VI-th stage of organogenesis.

                  TABLE 3                                                          ______________________________________                                                                  Steri-                                                                               Number of                                                                              Percentage                                             Number of lity  grains in                                                                              of grain                                               grains in percen-                                                                              ear in  setting in                                   Example   ear under tage, open pol-                                                                              open polli-                             No.  No.       isolator  %     lination                                                                               nation, %                               1    2         3         4     5       6                                       ______________________________________                                         1.   Control   38.1       0.0  34.9    100.0                                   2.   Example 24                                                                               3.9       83.7  30.6    87.7                                    3.   Example 25                                                                               0.0       100.0 33.9    97.1                                    4.   Example 26                                                                               0.0       100.0 31.8    91.1                                    5.   Example 27                                                                               0.0       100.0 32.0    91.7                                    6.   Example 28                                                                               0.7       97.8  30.4    87.1                                    7.   Example 29                                                                               0.3       99.1  33.7    96.6                                    ______________________________________                                    

EXAMPLES 30-41

Plants of spring wheat of Moskovskaya 35 variety are treated at the VI-th stage of organogenesis (after Kuperman) with a 2% aqueous emulsion of the following sterilizing agents: diethyl-N-methyl-α-aminobenzylphosphonate, diethyl-N-phenyl-α-aminofurylmethylphosphonate, dimethyl-N-ethyl-α-aminobenzylphosphonate, dimethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-α-amino-α-methylpropylphosphonate, dimethylphosphite, diammoniumphosphite, diethyl-N-ethyl-α-aminofurylmethylphosphonate, methylammoniummonobutylphosphite, diethyl-N, N-dimethylamidophosphate, diisopropyl-N-methyl-α-aminofurylmethylphosphonate respectively. As the emulsifying agent, 0.1% by mass of calcium C₁₂ -C₁₄ -alkylbenzenesulphonate is added, and as the adjuvant -0.1% by mass of dimethylformamide. The rate of consumption of the preparation is 10 kg/ha. Serving as the control are the plants treated with the diluent without the sterilizing agent. The results of the tests are shown in Table 4. Similar results are obtained in the treatment of the plants at the V-th stage of organigenesis.

                  TABLE 4                                                          ______________________________________                                                                  Steri-        Percentage                                             Number of lity  Number of                                                                              of grain                                               grains in percen-                                                                              grains in                                                                              setting in                                   Example   ear under tage, ear in open                                                                            open polli-                             No.  No.       isolator  %     pollination                                                                            nation, %                               1    2         3         4     5       6                                       ______________________________________                                         1.   Control   27.5       0.0  33.2    100.0                                   2.   Example 30                                                                               0.0       100.0 29.8    89.8                                    3.   Example 31                                                                               0.1       99.4  30.1    90.7                                    4.   Example 32                                                                               0.6       97.8  30.6    92.2                                    5.   Example 33                                                                               1.3       95.2  28.8    86.7                                    6.   Example 34                                                                               0.1       99.4  29.1    87.6                                    7.   Example 35                                                                               0.1       99.4  31.5    94.9                                    8.   Example 36                                                                               0.0       100.0 28.4    85.5                                    9.   Example 37                                                                               0.4       98.5  32.3    97.3                                    10.  Example 38                                                                               0.0       100.0 30.7    92.5                                    11.  Example 39                                                                               6.0       78.0  32.0    96.4                                    12.  Example 40                                                                               1.2       95.6  28.9    87.0                                    13.  Example 41                                                                               0.1       99.4  30.6    92.2                                    ______________________________________                                    

EXAMPLES 42-47

Plants of spring wheat of Botanicheskaya 4 variety are treated at the VI-th stage of organogenesis (after Kuperman) with a 2% aqueous emulsion of the following sterilizing agents: diethyl-α-hydroxyfurylmethylphosphonate, diethyl-N, N-dimethylamidophosphate, diethyl-N-methyl-α-aminofurylmethylphosphonate, diethylphosphite, diethyl-N-ethyl-α-aminofurylmethylphosphonate, diisopropyl-N-methyl-α-aminofurylmethylphosphonate respectively. As the emulsifying agent 0.1% by mass of calcium C₁₂ -C₁₄ -alkylbenzenesulphonate is added, as the adjuvant -0.1% by mass of dimethylsulphoxide. The rate of consumption of the preparation is 8 kg/ha. Serving as the control are the plants treated in a manner similar to that described in Examples 30 to 41. The results of the tests are shown in Table 5. Similar results are obtained in the treatment of the plants at the V-th stage of organogenesis.

                  TABLE 5                                                          ______________________________________                                                                  Steri-        Percentage                                             Number of lity  Number of                                                                              of grain                                               grains in percen-                                                                              grains in                                                                              setting in                                   Example   ear under tage, ear in open                                                                            open polli-                             No.  No.       isolator  %     pollination                                                                            nation, %                               1    2         3         4     5       6                                       ______________________________________                                         1.   Control   28.2       0.0  30.1    100.0                                   2.   Example 42                                                                               0.0       100.0 27.8    92.4                                    3.   Example 43                                                                               0.1        99.7 28.1    93.4                                    4.   Example 44                                                                               0.0       100.0 28.8    95.7                                    5.   Example 45                                                                               0.3        98.9 26.5    88.0                                    6.   Example 46                                                                               0.0       100.0 23.6    78.1                                    7.   Example 47                                                                               0.1        99.7 28.4    94.4                                    ______________________________________                                    

EXAMPLES 48-54

Plants of triticale of PRAG-109 variety are treated at the VI-th stage of organogenesis (after Kuperman) with a 2% aqueous emulsion of the following sterilizing agents: diethyl-N-phenyl-α-aminofurylmethylphosphonate, dimethyl-N-ethyl-α-aminobenzylphosphonate, diethyl-N-methyl-2-aminofurylmethylphosphonate, diethyl-N, N-dimethylamidophosphate, diethyl-α-aminoethylphosphonate, diethyl-N-ethyl-α-aminofurylmethylphosphonate, diisopropyl-N-methyl-α-aminofurylmethylphospohnate respectively. As the emulsifying agent 0.1% by mass of calcium C₁₂ -C₁₄ -alkylbenzenesulphonate is added, as the adjuvant - 0.01% by mass of tetrahydrofuran. The rate of consumption of the preparation is 20 kg/ha. Serving as the control are the plants treated in a manner similar to that described in Example I hereinabove. The results of these tests are shown in Table 6 hereinbelow. Similar results are obtained in the treatment of the plants at the V-th stage of organogenesis.

                  TABLE 6                                                          ______________________________________                                                                  Steri-        Percentage                                             Number of lity  Number of                                                                              of grain                                               grains in percen-                                                                              grains in                                                                              setting in                                   Example   ear under tage, ear in open                                                                            polli-                                  No.  No.       isolator  %     pollination                                                                            nation, %                               1    2         3         4     5       6                                       ______________________________________                                         1.   Control   62.2       0.0  69.0    100.0                                   2.   Example 48                                                                               0.0       100.0 58.8    85.2                                    3.   Example 49                                                                               0.1       99.7  63.1    91.4                                    4.   Example 50                                                                               0.0       100.0 61.6    89.3                                    5.   Example 51                                                                               0.8       98.7  66.2    95.9                                    6.   Example 52                                                                               2.6       96.8  61.1    88.6                                    7.   Example 53                                                                               0.6       99.0  60.8    88.1                                    8.   Example 54                                                                               1.1       98.2  64.5    93.5                                    ______________________________________                                    

EXAMPLES 55.57

Plants of triticale of Amphidiploid-206 variety are treated, in a manner similar to that described in Example 60, at the V-th and VI-th stages of organogenesis with a 2% aqueous emulsion of the following sterilizing agents: diethyl-α-aminoethylphosphonate, diethyl-N-ethyl-α-aminofurylmethylphosphonate, diisopropyl-N-methyl-α-aminofurylmethylphosphonate respectively. The rate of consumption of the preparation is 12 kg/ha. The results of the tests are shown in Table 7 hereinbelow.

                  TABLE 7                                                          ______________________________________                                                                  Steri-                                                                               Number of                                                                              Percentage                                             Number of lity  grains in                                                                              of grain                                               grains in percen-                                                                              ear in  setting in                                   Example   ear under tage, open polli-                                                                            open polli-                             No.  No.       isolator  %     nation  nation, %                               1    2         3         4     5       6                                       ______________________________________                                         1.   Control   31.7       0.0  36.6    100.0                                   2.   Example 55                                                                               0.0       100.0 30.5    83.3                                    3.   Example 56                                                                               0.0       100.0 33.8    92.3                                    4.   Example 57                                                                               0.0       100.0 32.9    89.9                                    ______________________________________                                    

EXAMPLES 58-69

Plants of tetrapolid rye of Belta variety are treated in a manner similar to that described in Example I hereinabove with a 2% aqueous emulsion of the following sterilizing agents: diethyl-N-methyl-α-aminobenzylphosphonate, diethyl-N-phenyl-α-aminofurylmethylphosphonate, dimethyl-N-ethyl-α-aminobenzylphosphonate, dimethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-α-amino-α-methylpropylphosphonate, diisopropylphosphite, diethyl-N, N-dimethylamidophosphate, diethyl-N-methyl-=α-aminofurylmethylphosphonate, diethyl-α-aminoethylphosphonate, diethyl-N-ethyl-α-aminofurylmethylphosphonate, diisopropyl-N-methyl-α-aminofurylmethylphosphonate respectively. Serving as the control are the plants treated in a manner similar to that described in Example I hereinabove. The rate of consumption of the preparation is 12 kg/ha. THe results of the tests are shown in Table 8 hereinbelow.

                  TABLE 8                                                          ______________________________________                                                                                Percentage                                                       Steri-                                                                               Number of                                                                              of grain                                               Number of lity  grains in                                                                              setting in                                             grains in percen-                                                                              ear in  open pol-                                    Example   ear under tage, open polli-                                                                            lination,                               No.  No.       isolator  %     nation  %                                       1    2         3         4     5       6                                       ______________________________________                                         1.   Control   43.3       0.0  47.1    100.0                                   2.   Example 58                                                                               1.0       97.7  40.8    86.6                                    3.   Example 59                                                                               0.1       99.8  42.1    89.4                                    4.   Example 60                                                                               0.0       100.0 36.4    77.3                                    5.   Example 61                                                                               0.1       99.8  43.5    92.4                                    6.   Example 62                                                                               0.2       99.5  44.3    94.0                                    7.   Example 63                                                                               0.0       100.0 45.9    97.4                                    8.   Example 64                                                                               3.1       92.8  42.8    90.9                                    9.   Example 65                                                                               0.8       98.2  45.8    97.2                                    10.  Example 66                                                                               2.5       94.2  32.5    69.0                                    11.  Example 67                                                                               0.0       100.0 44.2    93.8                                    12.  Example 68                                                                               0.7       98.4  37.6    79.8                                    13.  Example 69                                                                               0.0       100.0 42.5    90.2                                    ______________________________________                                    

EXAMPLES 70-80

Plants of diploid rye of Chulpan variety are treated at the VI-th stage of organogenesis with a 2% aqueous emulsion of the following sterilizing agents: diethyl-N-methyl-α-aminobenzylphosphonate, diethyl-N-phenyl-α-aminofurylmethylphosphonate, dimethyl-N-ethyl-α-aminobenzylphosphonate, dimethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-α-amino-α-methylpropylphosphonate, diethyl-N, N-dimethylamidophosphate, diethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-α-aminoethylphosphonate, diethyl-N-ethyl-α-aminofurylmethylphosphonate, diisopropyl-N-methyl-α-aminofurylmethylphosphonate, respectively. As the emulsifying agent 0.1% by mass of calcium alkyl (C₁₂ -C₁₄)-benzenesulphonate and as the adjuvant - 0.01% by mass of dimethylformamide. The rate of consumption of the preparation. Serving as the control are the plants treated in a manner similar to that described in Example I. The results of the tests are shown in Table 9. Similar results are obtained in the treatment of the plants at the V-th stage of organogenesis.

                  TABLE 9                                                          ______________________________________                                                                                Percen-                                                                        tage of                                                          Sterili-      grain                                                  Number of ty per-                                                                              Number of                                                                              setting                                                grains in cen-  grains in                                                                              in open                                      Example   ear under tage, ear in open                                                                            pollina-                                No.  No.       isolator  %     pollination                                                                            tion, %                                 1    2         3         4     5       6                                       ______________________________________                                         1.   Control   57.1       0.0  64.7    100.0                                   2.   Example 70                                                                               0.3       99.5  61.8    95.5                                    3.   Example 71                                                                               0.1       99.8  60.6    93.7                                    4.   Example 72                                                                               0.0       100.0 54.8    84.7                                    5.   Example 73                                                                               0.6       99.0  58.1    89.8                                    6.   Example 74                                                                               0.4       99.3  62.6    96.8                                    7.   Example 75                                                                               0.0       100.0 57.4    88.7                                    8.   Example 76                                                                               0.7       98.8  60.7    93.8                                    9.   Example 77                                                                               0.0       100.0 59.4    91.8                                    10.  Example 78                                                                               0.9       98.4  62.3    96.3                                    11.  Example 79                                                                               0.7       98.8  63.8    98.6                                    12.  Example 80                                                                               0.0       100.0 61.6    95.2                                    ______________________________________                                    

EXAMPLES 81-92

Plants of diploid rye of Kharkovskaya-55 variety are treated at the VI-th stage of organogenesis with a 2% aqueous emulsion of the following sterilizing agents: diethyl-N-methyl-α-aminobenzylphosphonate, diethyl-N-phenyl-α-aminofurylmethylphosphonate, dimethyl-N-α-ethyl-α-aminobenzylphosphonate, dimethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-α-amino-α-methylpropylphosphonate, dimethylphosphite, diethyl-N, N-dimethylamidophosphate, diethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-α-aminoethylphosphonate, diethyl-N-ethyl-α-aminofurylmethylphosphonate, diisopropyl-N-methyl-α-aminofurylmethylphosphonate respectively. As the emulsifying agent 0.1% by mass of calcium C₁₂ -C₁₄ -alkylphosphonate is added, as the adjuvant - 0.01% by mass of dodecylsulphate. The rate of consumption of the preparation is 12 kg/ha. Serving as the control are the plants treated in a manner similar to that described in Example I hereinbefore. The results of the tests are shown in Table 10 hereinbelow. Similar results are obtained in the treatment of the plants at the V-th stage of organogenesis.

                  TABLE 10                                                         ______________________________________                                                                                 Percen-                                                                        tage of                                                                        grain                                                 Number of        Number of                                                                              setting                                               grains in Sterility                                                                             grains in                                                                              in open                                     Example   ear under percen-                                                                               ear in open                                                                            pollina-                               No.  No.       isolator  tage, %                                                                               pollination                                                                            tion, %                                ______________________________________                                         1.   Control   38.4       0.0   46.8    100.0                                  2.   Example 81                                                                               0.0       100.0  40.6    86.8                                   3.   Example 82                                                                               0.2       99.5   42.5    90.8                                   4.   Example 83                                                                               0.0       100.0  39.8    85.0                                   5.   Example 84                                                                               0.7       98.2   44.1    94.2                                   6.   Example 85                                                                               0.0       100.0  32.6    69.6                                   7.   Example 86                                                                               0.1       99.7   43.7    93.4                                   8.   Example 87                                                                               0.0       100.0  40.4    86.3                                   9.   Example 88                                                                               0.6       98.4   44.3    94.7                                   10.  Example 89                                                                               0.7       98.2   40.8    87.2                                   11.  Example 90                                                                               0.0       100.0  44.9    95.9                                   12.  Example 91                                                                               0.2       99.5   40.2    85.9                                   13.  Example 92                                                                               0.0       100.0  39.5    84.4                                   ______________________________________                                    

EXAMPLES 93-102

Plants of millet of Mironovskoye 94 variety are treated in a manner similar to that of Example 14 with a 1% aqueous emulsion of the following sterilizing agents: diethyl-N-phenyl-α-aminofurylmethylphosphonate, dimethyl-N-ethyl-α-aminobenzylphosphonate, dimethyl-N-methyl-α-aminofurylphosphonate, diethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-α-amino-α-methylpropylphosphonate, diethyl-N, N-dimethylamidophosphate, diethyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-α-aminoethylphosphonate, diethyl-Methyl-α-aminofurylmethylphosphonate, diisopropyl-N-methyl-α-aminofurylmethylphosphonate respectively. The rate of consumption of the preparation is 6 kg/ha. The results are shown in Table II.

                  TABLE 11                                                         ______________________________________                                                                         Number of                                                                              Percen-                                                Number of Steri-                                                                               grains in                                                                              tage of                                                grains in lity  panicle setting                                                panicle   percen-                                                                              in open in open                                     Example    under iso-                                                                               tage, pollina-                                                                               pollina-                               No.  No.        lator     %     tion    tion, %                                ______________________________________                                         1    Control    320.5      0.0  379.5   100                                    2.   Example 93 0.0       100.0 315.6   83.2                                   3.   Example 94 0.0       100.0 294.8   77.7                                   4.   Example 95 0.0       100.0 326.4   86.0                                   5.   Example 96 0.0       100.0 301.5   79.4                                   6.   Example 97 0.0       100.0 359.2   94.6                                   7.   Example 98 0.0       100.0 300.7   79.2                                   8.   Example 99 0.0       100.0 348.6   91.8                                   9.   Example 100                                                                               0.0       100.0 284.3   74.9                                   10.  Example 101                                                                               0.0       100.0 352.5   92.9                                   11.  Example 102                                                                               0.0       100.0 362.9   95.6                                   ______________________________________                                    

EXAMPLES 103-111

Plants of millet of Kormovoye-I variety are treated in a manner similar to that described in Example I hereinabove with a 1% aqueous emulsion of the following sterilizing agents: diethyl-N-phenyl-α-aminofurylmethylphosphonate, diethylphosphite, diisopropylphosphite, dimethylammoniummonomethylphosphite, diethyl-α-hydroxyfurylmethylphosphonate, diethyl-N, N-dimethylamidophosphate, diethyl-α-aminoethylphosphonate, diethyl-N-ethyl-2-aminofurylmethylphosphonate, diisopropyl-N-methyl-α-aminofurylmethylphosphonate respectively. The rate of consumption of the preparation is 6 kg/ha. The results of the tests are shown in Table 12 hereinbelow.

                  TABLE 12                                                         ______________________________________                                                                                 Percen-                                                Number of Sterili-                                                                             Number of                                                                              tage of                                                grains in ty per-                                                                              grains in                                                                              setting                                                panicle   cen-  panicle in                                                                             in open                                     Example    under iso-                                                                               tage, open polli-                                                                            pollina-                               No.  No.        lator     %     nation  tion                                   ______________________________________                                         1.   Control    125.0      0.0  146.7   100.0                                  2.   Example 103                                                                               0.0       100.0 125.6   85.6                                   3.   Example 104                                                                               0.0       100.0 138.9   94.7                                   4.   Example 105                                                                               0.0       100.0 120.2   81.9                                   5.   Example 106                                                                               0.0       100.0 118.6   80.8                                   6.   Example 107                                                                               0.0       100.0 134.7   91.8                                   7.   Example 108                                                                               0.0       100.0 112.4   76.6                                   8.   Example 109                                                                               0.0       100.0 131.8   89.8                                   9.   Example 110                                                                               0.0       100.0 127.7   87.0                                   10.  Example 111                                                                               0.0       100.0 135.4   92.3                                   ______________________________________                                    

EXAMPLES 112-118

Plants of sunflower of Peredovik variety, VNIIMK 8931 variety and BK-119 line are treated in a manner similar to that described in Example I hereinbefore with a 1% aqueous emulsion of the following sterilizing agents: diethyl-α-aminoethylphosphonate, diethyl-N-ethyl-α-aminofurylmethylphosphonate, diisopropyl-N-methyl-α-aminofurylmethylphosphonate, diethyl-α-aminoethylphosphonate, diethyl-N, N-dimethylamidophosphate, diethyl-α-aminoethylphosphonate, diethyl-N-phenyl-α-aminofuryl-αmethylphosphonate respectively. The rate of consumption of the preparation is 6 kg/ha. The test results are shown in Table 13.

                  TABLE 13                                                         ______________________________________                                                                 Setting                                                                        of ache-     Oil-                                                      Steri-  nes in Mass  con-  Ener-                                               lity    open   of    tent  gy                                                  percen- polli- 1,000 of-   of                                       Example    tage,   nation,                                                                               achen-                                                                               achen-                                                                               growth                              No.  No.        %       %      es, g es, % %                                   ______________________________________                                         Sunflower of Peredovik variety                                                 1.   Control    0.2     85.0   84.0  54.7  100                                 2.   Example 112                                                                               100     84.2   84.3  52.2  100                                 3.   Example 113                                                                               100     83.3   110.0 54.9  100                                 4.   Example 114                                                                               100     81.8   83.4  52.8  100                                 Sunflower of VNIIMK 8931 variety                                               5.   Control    0.5     85.7   83.0  54.7  100                                 6.   Example 115                                                                               100     84.2   83.7  55.1  100                                 7.   Example 116                                                                               100     83.6   84.2  54.0  100                                 Sunflower of BK-119 line                                                       8.   Control    2.0     85.0   60.0  51.0  100                                 9.   Example 117                                                                               100     82.3   58.6  52.8  100                                 10.  Example 118                                                                               100     83.8   61.4  51.6  100                                 ______________________________________                                    

EXAMPLES 119-122

Plants of winter wheat Mironovskaya 808 variety are treated at the V-th stage of organogenesis with a 2% aqueous emulsion of the following mixtures of sterilizing agents (employed in the ratio I:I): diisopropyl-N-methyl-α-aminofurylmethylphosphonate and dimethylphosphite, diethyl-N-methyl-α-aminofurylmethylphosphonate and diethyl-α-aminoethylphosphonate, diethyl-N, N-dimethylamidophosphate and methylammoniummonobutylphosphite, diethyl-N-phenyl-α-aminofurylmethylphosphonate and diethylphosphate respectively. As the emulsifying agent 0.1% by mass of calcium C₁₂ -C₁₄ -alkylbenzenesulphonate is added, as the adjuvant - 0.01% by mass of dodecylsulphate. The rate of consumption of the preparation is 12 kg/ha. Serving as the control are the plants treated in a manner similar to that described in Example I. The results of the tests are shown in Table 14 hereinbelow. Similar results are obtained in the treatment of the plants at the VI-th stage of organogenesis.

                  TABLE 14                                                         ______________________________________                                                                                 Percen-                                                                        tage of                                                          Per-  Number of                                                                              grain set-                                             Number of cen-  grains in                                                                              ting in                                                grains in tage of                                                                              ear in  open                                        Example    ear under steri-                                                                               open pol-                                                                              polli-                                 No.  No.        isolator  lity, %                                                                              lination                                                                               nation, %                              ______________________________________                                         1.   Control    38.3      0.0   41.0    100.0                                  2.   Example 119                                                                               0.0       100   39.2    95.6                                   3.   Example 120                                                                               0.0       100   38.6    94.1                                   4.   Example 121                                                                               0.0       100   40.8    99.5                                   5.   Example 122                                                                               0.0       100   39.7    96.8                                   ______________________________________                                    

EXAMPLES 123-124

Plants of spring wheat of Moskovskaya 35 variety are treated at the V-th stage of organogenesis with a 1% aqueous emulsion of the following mixtures of sterilizing agents (employed in the ratio I:I): diethyl-N-ethyl-α-aminofurylmethylphosphonate and diethyl-N-methyl-α-aminofurylmethylphosphonate; dimethyl-N-methyl-α-aminofurylmethylphosphonate and dimethylphosphite respectively. As the emulsifying agent 0.1% by mass of calcium C₁₂ -C₁₄ -alkylbenzene sulphonate is added, as the adjuvant - 0.01% by mass of dimethylsulphoxide. Serving as the control are the plants treated in a manner similar to that described in Example I hereinbefore. The rate of consumption of the preparation is 6 kg/ha. The results of the tests are shown in Table 15. Similar results are obtained in the treatment of plants at the VI-th stage of organogenesis.

                  TABLE 15                                                         ______________________________________                                                                                 Percen-                                                                        tage of                                                          Steri-        grain set-                                             Number of lity  Number of                                                                              ting in                                                grains in percen-                                                                              grains in                                                                              open pol-                                   Example    ear under tage, ear in open                                                                            lination,                              No.  No.        isolator  %     pollination                                                                            %                                      ______________________________________                                         1.   Control    27.5      0.0   33.2    100                                    2.   Example 123                                                                               0.0       100   30.6    92.2                                   3.   Example 124                                                                               0.0       100   31.8    95.8                                   ______________________________________                                    

EXAMPLES 125-128

Plants of triticale of PRAG - 109 variety are treated at the V-th stage of organogenesis with a 2% aqueous emulsion of the following mixtures of sterilizing agents (employed in the ratio 1:1): diethyl-N-phenyl-α aminofurylmethylphosphonate and diethylphosphite, diethyl-N-methyl-α-aminobenzenephosphonate and diethyl-α-aminoethylphosphonate, diethyl-N, N-dimethylamidophosphate and dimethylphosphite, diammoniumphosphite and diethyl-N-methyl-α-aminofurylmethylphosphonate respectively. As the emulsifying agent 0.1% by mass of calcium C₁₂ -C₁₄ -alkylbenzenesulphonate is added, as the adjuvant 0.01% by mass of tetrahydrofuran. The rate of consumption of the preparation is 12 kg/ha. Serving as the control are the plants treated ion a manner similar to that described in Example I hereinbefore. The test results are shown in Table 16 hereinbelow. Similar results are obtained in the treatment of the plants at the VI-th stage of organogenesis.

                  TABLE 16                                                         ______________________________________                                                                                 Percen-                                                                        tage of                                                          Steri-                                                                               Number of                                                                              grain set-                                             Number of lity  grains in                                                                              ting in                                                grains in percen-                                                                              ear in  open pol-                                   Example    ear under tage, open polli-                                                                            lination,                              No.  No.        isolator  %     nation  %                                      ______________________________________                                         1.   Control    62.2      0.0   69.0    100                                    2.   Example 125                                                                               0.0       100   63.4    92.0                                   3.   Example 126                                                                               0.0       100   60.1    87.1                                   4.   Example 127                                                                               0.0       100   59.8    86.7                                   5.   Example 128                                                                               0.0       100   62.2    90.1                                   ______________________________________                                    

INDUSTRIAL APPLICABILITY

The method according to the present invention is useful in selection and seed production of highly productive grades and hydrides of crops. 

We claim:
 1. A method of sterilizing anthers of plants by way of treatment thereof with a sterilizing agent in combination with a diluent during the period of the fifth and/or sixth stage of organogenesis, comprising to said anthers a sterilizing agent made of derivatives of phosphoric acids or mixtures thereof of the general formula: ##STR4## wherein R is H, a C₁ -C₄ -alkoxy, dimethylamine, wherein X is O, NH; B is H, a C₁ -C₄ -alkyl, phenyl; D is H, CH₃ ; A is a C₁ -C₄ -alkyl, phenyl, furyl; R¹ is OH, ONH₄, OAlk(C₁ -C₄), phenyl; R² is a C₁ -C₄ -alkyl; NaNH₄, NH₃ Alk(C₁ -C₄), NH₂ Alk₂ (C₁ -C₄).
 2. A method according to claim 1 wherein said derivatives of phosphoric acids are used in combination with a diluent.
 3. A method according to either claims 1-2, wherein the plants to be treated with said sterilizing agent are graminous plants or sunflower plants.
 4. A method according to either claims 1 or 2, wherein at least one further application of the sterilizing agent is applied during the periods of the fifth and/or sixth stage of organogenesis to ensure a high level of sterilization of said anthers. 